Ethyl crotonate

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  • Identifiers

    CAS number
    623-70-1

    Molecular formula
    C6H10O2

    SMILES
    CCOC(=O)/C=C/C

    Safety labels

    Flammable
    Flammable

    Irritant
    Irritant

    Retention indicies (RI)

    • Carbowax: 1171.0

  • Odor profile

    Fruity 93.49%
    Ethereal 61.3%
    Apple 60.76%
    Sweet 59.87%
    Rummy 55.75%
    Green 52.08%
    Pungent 51.71%
    Pineapple 50.15%
    Sharp 49.9%
    Winey 44.87%

    Scent© AI

  • Properties

    XLogP3-AA
    1.3

    pKa est.
    7.89 (neutral)

    Molecular weight
    114.14 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    140°C

    Flash point est.
    24.94 ˚C

    Solubility expt.

    • Insoluble in water; soluble in oils
    • Soluble (in ethanol)

  • Synonyms

    • ETHYL CROTONATE
    • 623-70-1
    • ethyl (E)-but-2-enoate
    • 2-Butenoic acid, ethyl ester, (2E)-
    • Ethyl trans-2-butenoate
    • 10544-63-5
    • Ethyl trans-crotonate
    • Ethyl (E)-crotonate
    • 2-Butenoic acid, ethyl ester
    • Crotonic acid, ethyl ester
    • ethyl (2E)-but-2-enoate
    • Crotonic acid, ethyl ester, (E)-
    • Ethyl (E)-2-butenoate
    • 2-Butenoic acid, ethyl ester, (E)-
    • Ethyl crotonate (E)
    • FEMA No. 3486
    • trans-2-Butenoic acid ethyl ester
    • (E)-ethyl crotonate
    • Crotonic acid ethyl ester
    • (E)-2-Butenoic acid ethyl ester
    • Ethyl 2-butenoate
    • 99YUC7A1X1
    • (E)-but-2-enoic acid ethyl ester
    • Ethylester kyseliny krotonove
    • Crotonate d'ethyle, (E)-
    • Ethyl 2-butenoate, (E)-
    • (E)-Ethyl but-2-enoate
    • Ethyl (2E)-2-butenoate
    • NSC 4778
    • EINECS 210-808-7
    • EINECS 234-125-9
    • UN1862
    • Ethylester kyseliny krotonove [Czech]
    • (E)-CH3CH=CHCOOC2H5
    • alpha-Crotonic acid ethyl ester, (E)-
    • BRN 0635834
    • BRN 1720418
    • NSC4778
    • UNII-99YUC7A1X1
    • AI3-05622
    • Trans-ethylcrotonate
    • MFCD00009289
    • ethyl trans crotonate
    • Ethyl crotonate, 96%
    • Ethyl crotonate, 99%
    • Crotonate d'ethyle, E-
    • crotonic-acid-ethyl-ester
    • Ethyl(E)-but-2-enoate
    • SCHEMBL24483
    • 77825-56-0
    • Ethyl (2E)-2-butenoate #
    • ETHYL CROTONATE [FHFI]
    • ETHYL-(E)-2-BUTENOATE
    • ETHYL-TRANS-2-BUTENOATE
    • CHEMBL3273403
    • DTXSID5057591
    • ETHYL TRANS-2-BUTENOATE-
    • CHEBI:173393
    • trans-but-2-enoic acid ethyl ester
    • BBL027753
    • STL146343
    • AKOS005721070
    • CROTONIC ACID ETHYL ESTER [MI]
    • ETHYL-(E)-2-BUTENOATE [FCC]
    • Ethyl trans-2-butenoate, >=96%, FG
    • TRANS-2-BUTENOIC ACID ETHYLESTER
    • .alpha.-Crotonic acid ethyl ester, trans-
    • DB-029759
    • NS00075573
    • EN300-344919
    • Ethyl crotonate [UN1862] [Flammable liquid]
    • Ethyl trans-2-butenoate, natural, >=97%, FG
    • A833743
    • Q1141618
    • Z2327209524
    • InChI=1/C6H10O2/c1-3-5-6(7)8-4-2/h3,5H,4H2,1-2H3/b5-3

  • Applications

    Ethyl trans-2-butenoate (CAS 623-70-1) is a key fruity ester used extensively in flavour and fragrance formulations because of its vivid pineapple, apple and strawberry nuances; it is added to candies, beverages, yogurts, baked goods, tobacco substitutes and compound flavours to sharpen, sweeten or recreate fresh fruit notes while keeping costs lower than natural extracts; in perfumery and personal-care products it is blended with tropical and citrus accords to impart a bright, youthful lift to perfumes, creams and shampoos; in chemical and pharmaceutical manufacturing it serves as a versatile intermediate for the preparation of butenoic derivatives, amino acids and heterocyclic scaffolds, thereby expanding structural libraries for drug discovery and agrochemical research; owing to its volatility and reactivity it is also employed as a GC-MS aroma reference standard, a tracer in aroma metabolism studies, a selective reaction solvent, a comonomer for functional copolymers, and a biological attractant for trapping pest insects in organic farming, illustrating the multi-sector relevance of this compact yet highly adaptable ester.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 991.7
    methanol 1229.34
    isopropanol 789.47
    water 4.73
    ethyl acetate 808.41
    n-propanol 773.77
    acetone 1154.21
    n-butanol 697.53
    acetonitrile 1461.5
    DMF 1759.06
    toluene 374.7
    isobutanol 548.56
    1,4-dioxane 1193.46
    methyl acetate 874.07
    THF 1441.41
    2-butanone 836.2
    n-pentanol 566.31
    sec-butanol 733.25
    n-hexane 265.67
    ethylene glycol 263.1
    NMP 1699.57
    cyclohexane 401.95
    DMSO 1551.46
    n-butyl acetate 627.64
    n-octanol 501.95
    chloroform 2707.82
    n-propyl acetate 553.56
    acetic acid 1617.41
    dichloromethane 2764.71
    cyclohexanone 1272.09
    propylene glycol 329.26
    isopropyl acetate 425.05
    DMAc 1179.49
    2-ethoxyethanol 596.12
    isopentanol 476.77
    n-heptane 163.59
    ethyl formate 647.36
    1,2-dichloroethane 1359.62
    n-hexanol 564.63
    2-methoxyethanol 1006.75
    isobutyl acetate 297.27
    tetrachloromethane 399.72
    n-pentyl acetate 452.83
    transcutol 1438.21
    n-heptanol 284.31
    ethylbenzene 312.65
    MIBK 359.49
    2-propoxyethanol 701.57
    tert-butanol 843.26
    MTBE 510.42
    2-butoxyethanol 383.89
    propionic acid 972.17
    o-xylene 288.37
    formic acid 420.13
    diethyl ether 675.78
    m-xylene 268.17
    p-xylene 440.67
    chlorobenzene 826.73
    dimethyl carbonate 347.5
    n-octane 84.65
    formamide 526.04
    cyclopentanone 1343.73
    2-pentanone 671.23
    anisole 535.45
    cyclopentyl methyl ether 694.36
    gamma-butyrolactone 1670.79
    1-methoxy-2-propanol 782.72
    pyridine 1241.04
    3-pentanone 560.64
    furfural 1487.9
    n-dodecane 81.47
    diethylene glycol 516.71
    diisopropyl ether 212.88
    tert-amyl alcohol 688.18
    acetylacetone 698.19
    n-hexadecane 90.09
    acetophenone 547.49
    methyl propionate 719.59
    isopentyl acetate 451.23
    trichloroethylene 2643.36
    n-nonanol 401.59
    cyclohexanol 733.67
    benzyl alcohol 464.15
    2-ethylhexanol 374.25
    isooctanol 224.06
    dipropyl ether 413.33
    1,2-dichlorobenzene 758.92
    ethyl lactate 319.44
    propylene carbonate 949.27
    n-methylformamide 976.15
    2-pentanol 508.43
    n-pentane 212.81
    1-propoxy-2-propanol 534.51
    1-methoxy-2-propyl acetate 464.14
    2-(2-methoxypropoxy) propanol 465.21
    mesitylene 211.7
    ε-caprolactone 1084.02
    p-cymene 216.9
    epichlorohydrin 1489.8
    1,1,1-trichloroethane 1261.44
    2-aminoethanol 428.13
    morpholine-4-carbaldehyde 1226.04
    sulfolane 1976.48
    2,2,4-trimethylpentane 91.67
    2-methyltetrahydrofuran 1025.12
    n-hexyl acetate 858.36
    isooctane 73.13
    2-(2-butoxyethoxy)ethanol 617.9
    sec-butyl acetate 324.19
    tert-butyl acetate 415.78
    decalin 165.85
    glycerin 424.64
    diglyme 1009.45
    acrylic acid 957.52
    isopropyl myristate 296.02
    n-butyric acid 1036.14
    acetyl acetate 535.18
    di(2-ethylhexyl) phthalate 261.34
    ethyl propionate 541.16
    nitromethane 2054.11
    1,2-diethoxyethane 549.0
    benzonitrile 896.52
    trioctyl phosphate 208.9
    1-bromopropane 902.5
    gamma-valerolactone 1477.8
    n-decanol 289.43
    triethyl phosphate 263.27
    4-methyl-2-pentanol 245.43
    propionitrile 969.22
    vinylene carbonate 1093.64
    1,1,2-trichlorotrifluoroethane 1059.69
    DMS 531.32
    cumene 234.34
    2-octanol 288.91
    2-hexanone 576.54
    octyl acetate 407.95
    limonene 326.42
    1,2-dimethoxyethane 1048.85
    ethyl orthosilicate 229.98
    tributyl phosphate 280.83
    diacetone alcohol 470.0
    N,N-dimethylaniline 418.79
    acrylonitrile 1293.08
    aniline 496.95
    1,3-propanediol 578.62
    bromobenzene 937.67
    dibromomethane 1856.41
    1,1,2,2-tetrachloroethane 1861.04
    2-methyl-cyclohexyl acetate 388.48
    tetrabutyl urea 370.87
    diisobutyl methanol 199.52
    2-phenylethanol 412.39
    styrene 433.67
    dioctyl adipate 422.73
    dimethyl sulfate 574.57
    ethyl butyrate 503.29
    methyl lactate 389.72
    butyl lactate 369.37
    diethyl carbonate 416.96
    propanediol butyl ether 485.72
    triethyl orthoformate 332.01
    p-tert-butyltoluene 208.68
    methyl 4-tert-butylbenzoate 456.98
    morpholine 1266.39
    tert-butylamine 581.69
    n-dodecanol 223.59
    dimethoxymethane 820.01
    ethylene carbonate 765.39
    cyrene 403.08
    2-ethoxyethyl acetate 484.45
    2-ethylhexyl acetate 363.7
    1,2,4-trichlorobenzene 819.23
    4-methylpyridine 1168.88
    dibutyl ether 520.43
    2,6-dimethyl-4-heptanol 199.52
    DEF 889.01
    dimethyl isosorbide 677.35
    tetrachloroethylene 1184.53
    eugenol 467.0
    triacetin 615.29
    span 80 492.86
    1,4-butanediol 297.7
    1,1-dichloroethane 1480.09
    2-methyl-1-pentanol 456.85
    methyl formate 780.91
    2-methyl-1-butanol 501.7
    n-decane 125.31
    butyronitrile 969.06
    3,7-dimethyl-1-octanol 377.03
    1-chlorooctane 373.57
    1-chlorotetradecane 164.36
    n-nonane 135.25
    undecane 96.59
    tert-butylcyclohexane 147.05
    cyclooctane 113.66
    cyclopentanol 878.32
    tetrahydropyran 1154.69
    tert-amyl methyl ether 414.94
    2,5,8-trioxanonane 758.66
    1-hexene 617.96
    2-isopropoxyethanol 395.87
    2,2,2-trifluoroethanol 399.08
    methyl butyrate 750.95

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction

Botanical

Name CAS Botanical Proportion
Orange leaf, sweet (Israel) 3 Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.1%
Orange leaf, sweet (Israel) 1 Citrus sinensis (L.) Osbeck, cultivar Jaffa (Shamouti), fam. Rutaceae 0.08%
Orange leaf, sweet (Israel) 2 Citrus sinensis (L.) Osbeck, cultivar Ruby (Blood orange), fam. Rutaceae 0.11%
Mandarin leaf (Petitgrain mandarin.) (Israel) 4 Citrus reticulata Blanco, cultivar Maya, fam. Rutaceae 0.04%
Ambarella fruit (Brazil) Spondias cytherea Sonnerat, fam. Anarcardiaceae 0.35%